How it works: “As a lawyer or an accountant, you log into Blue J, and our software asks you 20 to 30 questions about your client’s situation. Our AI then compares your circumstances to prior cases and predicts how a court will rule. It’s right about 90 per cent of the time.”

Eureka moment: “My co-founders and I already had the idea for Blue J when I became a judge for the Watson challenge, a student competition using IBM’s AI technology. That was the catalyst. I’m a law professor at U of T, so after the challenge, I ran a course about tax law and computer science, and by the end of the course, we had built a clunky prototype.”

How much you spent initially: “I founded the company with two other U of T law professors, and we each put in a small amount of money to get it started. But the real investment was sweat equity—working weekends and evenings on top of our jobs at U of T.”

Your big-time backers: “We’ve raised several million dollars from Mistral Venture Partners, BDC Capital, big accounting firms and some angel investors we met through the Creative Destruction Lab at U of T.”

Past life: “I went right from undergrad to law school to grad school to a Supreme Court clerk job to a tenure-track teaching job.”

App you can’t live without: “Audible. I listen to nearly 150 books a year at double speed. I recently finished The Theory That Would Not Die by Sharon McGrayne.”

Your tech role model: “Charlie Munger, an investor with a law degree who’s worked for Warren Buffett for decades. I admire his approach to problem solving.”

Coolest thing in your office: “We have a company Ping-Pong ladder on our wall, a leaderboard of our employees.”

If you weren’t running a start-up: “I’d probably still be an academic, but in philosophy or economics.”

The best advice you’ve received: “A CEO has three primary jobs: hiring the best people, having enough cash and having the right strategy.”

The worst advice you’ve received: “ ‘Raise as much money as you can at all times.’ Having too much cash sitting around leads to bad decisions: over-hiring, spending money in suboptimal ways and giving away too much equity.”